Reaktion #1690

Reaktionsgleichung

2-methoxycarbonyl-(1RS,4aSR,8aSR)-perhydoisoquinoline-1-carboxylic acid t-butyl ester

sodium ethoxide

→

title compound

Ausbeute 95.2%

2-Methoxycarbonyl-(1RS,4aRS,8aRS)-perhydoisoquinoline-1-carboxylic acid ethyl ester

Ausbeute 95.2%

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was refluxed (24 h)
2. 2
   SonstigeThe organic solvent was evaporated in vacuo, ethyl acetate (400 mL) and water (100 mL)
3. 3
   workup.ADDITIONwas added to the residue
4. 4
   SonstigeThe organic layer was separated
5. 5
   Waschenwashed twice with water
6. 6
   Trocknendried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Einengenthe filtrate was concentrated in vacuo

Vorschrift

To a solution of 2-methoxycarbonyl-(1RS,4aSR,8aSR)-perhydoisoquinoline-1-carboxylic acid t-butyl ester (81.2 g, 273 mmol) in EtOH (500 mL) was added sodium ethoxide (21% in ethanol) (88.4 mL, 273 mmol) and the reaction mixture was refluxed (24 h). The organic solvent was evaporated in vacuo, ethyl acetate (400 mL) and water (100 mL) was added to the residue. The organic layer was separated, washed twice with water, dried (MgSO4), filtered, and the filtrate was concentrated in vacuo to afford an oil of pure title compound (70 g,0.95%); FAB-MS 270 (MH+); TLC Rf (A) 0.61.

Quelle